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Top Holiday Rentals in Portland

NEW LISTING Riverview Cabin home!
Fridge, microwave, oven, stovetop
NEW LISTING Riverview Cabin home!
9.6 out of 10, Exceptional, (35)
"We enjoyed our stay in a beautiful house with great views of the Mississippi River"
NEW LISTING Riverview Cabin home!
Secluded, Romantic, Family Friendly And Cozy, Last House In The Valley.
TV, DVD player, books, video library
Secluded, Romantic, Family Friendly And Cozy, Last House In The Valley.
10.0 out of 10, Exceptional, (351)
"Joan and Jerry have set the gold standard for a well-appointed home and excellent hospitality! We have stayed at a few home rentals in the past, and all were good, but this home was far beyond any of them. The kitchen was well stocked. The bedrooms were perfect for 7 adults and 2 small children. The home is well-maintained, and the property is beautiful. I would recommend this property without hesitation."
Secluded, Romantic, Family Friendly And Cozy, Last House In The Valley.
Eagle Valley Vista spacious, pet-friendly, close to parks, dark sky viewing
Exterior
Eagle Valley Vista spacious, pet-friendly, close to parks, dark sky viewing
10.0 out of 10, Exceptional, (6)
"Great place to enjoy the beautiful outdoors. Bluffs all around and trout streams everywhere. Loved it."
The price is £173
per night
7 Jun - 8 Jun
Eagle Valley Vista spacious, pet-friendly, close to parks, dark sky viewing
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Your Home Away From Home
Property grounds
Your Home Away From Home
9.6 out of 10, Exceptional, (123)
"Great space, great area, and so thankful this was pet friendly. The park down the road had a walking path that was perfect for our dogs to get out and exercise. Definitely hoping we will be welcomed back!"
Your Home Away From Home
Blakley Hobbit Large Cabin
Fridge, microwave, oven, stovetop
Blakley Hobbit Large Cabin
8.2 out of 10, Very good, (23)
"My son turned 10 and for his birthday wanted to go to a cabin and fish all wknd with a couple friends. This cabin was perfect, they could wake up and walk right out to the river and fish at their leisure."
The price is £135
per night
6 Jun - 7 Jun
Blakley Hobbit Large Cabin
Exquisite comfort for family and friends in the heart of Downtown Viroqua.
Fridge, microwave, oven, stovetop
Exquisite comfort for family and friends in the heart of Downtown Viroqua.
10.0 out of 10, Exceptional, (216)
"Great location and accommodations that have served our organization for the last 5 years. We will return."
Exquisite comfort for family and friends in the heart of Downtown Viroqua.
Marina getaway located on the back sloughs of the mighty Mississippi.
Property grounds
Marina getaway located on the back sloughs of the mighty Mississippi.
10.0 out of 10, Exceptional, (40)
"This VRBO in La Crosse, WI is hands down the best VRBO we have every stayed at. Emily was a wonderful host. Location was great. We will definetly be returning. We highly recommend this VRBO. Thank you!"
Marina getaway located on the back sloughs of the mighty Mississippi.
Fly Fishing in the Driftless Region - Bishop Creek Cabin with a View
Property grounds
Fly Fishing in the Driftless Region - Bishop Creek Cabin with a View
9.8 out of 10, Exceptional, (126)
"Small but cozy place. Was very peaceful and quiet at night. Looking forward to staying again in the future"
Fly Fishing in the Driftless Region - Bishop Creek Cabin with a View
Pet-friendly Bohemian Bungalow conveniently located in South La Crosse.
Private kitchen
Pet-friendly Bohemian Bungalow conveniently located in South La Crosse.
10.0 out of 10, Exceptional, (13)
"The house was exactly as advertised. Great communication. Would definitely book again."
The price is £168
per night
27 Jun - 28 Jun
Pet-friendly Bohemian Bungalow conveniently located in South La Crosse.
Blakley Hobbit Small Cabin
Property grounds
Blakley Hobbit Small Cabin
7.8 out of 10, Good, (31)
"We always have the best time here. The location is the absolutely best and the cabin is what you should expect for the very very reasonable price. I have stayed here maybe 5-6 times now, with kids & with friend and it never disappoints."
The price is £98
per night
5 Jun - 6 Jun
Blakley Hobbit Small Cabin
Beautiful secluded cabin with amazing country views
View from property
Beautiful secluded cabin with amazing country views
10.0 out of 10, Exceptional, (9)
"Loved this cozy house for a relaxing weekend with friends. Saw so many birds sitting in the lovely back deck!"
Beautiful secluded cabin with amazing country views
Driftless Area Country House: large deck, spring fed creek, Amish area
Property grounds
Driftless Area Country House: large deck, spring fed creek, Amish area
10.0 out of 10, Exceptional, (59)
"This place is everything I could hope for in a vacation rental. It was meticulously clean, well stocked, and located in such a quiet and beautiful part of Wisconsin. There was an abundant amount of clean towels and blankets. The house rules and checkout process were minimal unlike other places we have been. And the owner was only a text message away and a real person which is so much better than trying to communicate with a third party house managing service. Our family came for the purpose of...
Driftless Area Country House: large deck, spring fed creek, Amish area
Cabin in Beautiful Timber Coulee
Smart TV, fireplace
Cabin in Beautiful Timber Coulee
10.0 out of 10, Exceptional, (56)
"Wonderful"
Cabin in Beautiful Timber Coulee
'RiverSong' Waterfront La Crosse Home w/ Dock
Fridge, microwave, stovetop, dishwasher
'RiverSong' Waterfront La Crosse Home w/ Dock
10.0 out of 10, Exceptional, (67)
"Well managed property with privacy and the mighty Mississippi River. Very convenient for kayaking."
'RiverSong' Waterfront La Crosse Home w/ Dock
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.
Property grounds
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.
8.8 out of 10, Excellent, (67)
"We had a great time there. The fishing is great for bass. Family said, that they would like to stay there again."
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.
Cozy Newly Built Cabin with Scenic Views
Exterior
Cozy Newly Built Cabin with Scenic Views
10.0 out of 10, Exceptional, (28)
"This was my second stay at the cabin, and it was again fantastic. The cabin has everything you need. The bed is comfortable. The setting is peaceful. Chad is a wonderful host, and went out of his way to make my stay perfect. I'll be back."
Cozy Newly Built Cabin with Scenic Views
Historic Bank Building on the Elroy-Sparta State Trail
Exterior
Historic Bank Building on the Elroy-Sparta State Trail
9.8 out of 10, Exceptional, (42)
"We ran the marathon in Norwalk, from the entrance of the building to starting line was a 30 second walk. If you're going for the bike trail, thia ia the perfect place to stay."
Historic Bank Building on the Elroy-Sparta State Trail
Soaker Tub & Sunset Sugarloaf Retreat
Property grounds
Soaker Tub & Sunset Sugarloaf Retreat
Soaker Tub & Sunset Sugarloaf Retreat
Cozy, quaint, and charming 3 bedroom near campuses
Property grounds
Cozy, quaint, and charming 3 bedroom near campuses
9.8 out of 10, Exceptional, (8)
"Met expectations"
The price is £323
per night
9 Jun - 10 Jun
Cozy, quaint, and charming 3 bedroom near campuses
Up The Creek Cottage - Townhome In Coon Valley
Outdoor dining
Up The Creek Cottage - Townhome In Coon Valley
9.2 out of 10, Wonderful, (30)
"This was a great home base for our weekend activities. The food at the Stockyard was great and the bloodymarys too."
Up The Creek Cottage - Townhome In Coon Valley
Don't see what you're looking for?
See all available properties in Portland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Portland you may be interested in

Stoney Creek Hotel La Crosse - Onalaska
Interior
Stoney Creek Hotel La Crosse - Onalaska
2.5 star property
9.0 out of 10, Wonderful, (1376)
"Cabin feel "
The price is £97
per night
16 Jun - 17 Jun
Stoney Creek Hotel La Crosse - Onalaska
AmericInn by Wyndham West Salem
Indoor pool
AmericInn by Wyndham West Salem
2.5 star property
8.4 out of 10, Very good, (700)
"We had a late arrival and all went well when we arrived. Very accomidating"
The price is £62
per night
5 Jun - 6 Jun
AmericInn by Wyndham West Salem
Microtel Inn by Wyndham Onalaska/La Crosse
Exterior
Microtel Inn by Wyndham Onalaska/La Crosse
2.0 star property
7.6 out of 10, Good, (1007)
"The hotel was clean, staff was friendly. It was right off the highway in a good area. You could hear the cars on the highway and the air conditioner was loud. The tv also had screen issues. But for a decent price and just a rest overnight was fine for us."
The price is £54
per night
5 Jun - 6 Jun
Microtel Inn by Wyndham Onalaska/La Crosse
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as £98 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals close to the most popular sights in Portland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Portland has to offer?

Secluded, Romantic, Family Friendly And Cozy, Last House In The Valley.: This holiday home rental outside of Portland is located in a rural location, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Portland?

While exploring the area, visit family-friendly sights like Dregne's Scandinavian Gifts, or get outside and enjoy nature at Norskedalen Nature and Heritage Center. LaCrosse River Trail and La Crosse Fairgrounds Speedway are a couple of places you'll find in the wider area.

What are holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for families.

Recent reviews of Portland properties
Expedia verified reviews

Stay Suites

Stay Suites

5/5 Excellent
"Located near restaurants, grocery store, gas station and shopping. Good variety on breakfast opinions included. Friendly staff, pool, laundry and fitness facilities included at a fair price."
A verified traveller stayed at Stay Suites
Posted 2 days ago
Stay Suites